Triethylamine → HCID 10130538, compound

HRID 612448Notes

Reaction equation

HRID 612448 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[NH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)N>CN(C)C=O.O.C(OCC)(=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:8][N:3]1[CH2:4][C:5]2[C:7](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:6]1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 786452-Hydrazinopyridine

Product 1

HCID 10130538HCID 10130538, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (10.5 ml) was added to a solution of alpha, alpha'-dibromo-o-xylene (10 g) and 2-hydrazinopyridine (4.1 g) in dimethylformamide. The mixture was stirred, under nitrogen, at ambient temperature for about 20 mins and diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. Trituration of the residue with ethyl acetate gave 3.8 g (48%) of product. Recrystallization of the product from ethyl acetate afforded the analytical sample, mp 130-131° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e5ae43d7036c4708b6423f1f8012bbee
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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